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Am I actually reading that they spent 33.33% or $220k of their investor money on printing t shirts?

Would be about one month of their revenue at current if you want to believe my quick estimate.

The absolute lowest it can be with their public pricing is:

9264 users on the annual family plan at $3/user/month = 27792

10799 users on the annual starter plan at $4.50/user/month = 48595.5

Total: $76387.5

My understanding is that the vast majority of their revenue is used to pay Google and Microsoft for access to their indexes though.

Oooh. And here I was wondering how the heck such a small team could build their own indexes.

The retail price you pay them is unlikely the wholesale price they pay the factory.